Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond - Université de Lorraine Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2014

Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond

Résumé

delta-Azaproline, a new bis-nitrogen proline surrogate has been used in order to control the conformation of an AA-Psi Pro bond. Conformational analysis of Xaa(1)-delta-azaPro-Xaa(3) performed by NMR, IR experiments, and molecular modeling revealed a preference for a trans conformation of the Xaa(1)-delta-azaPro bond when delta-azaPro is protected by a Boc group. The removal of the Boc protection leads to the establishment of a C-10 pseudocycle via a hydrogen bond network favoring the cis conformation of the Xaa(1)-delta-azaPro bond.
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hal-01498198 , version 1 (29-03-2017)

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Emelyne Humbert-Voss, Axelle Arrault, Brigitte Jamart-Grégoire. Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond. Tetrahedron, 2014, 70 (2), pp.363-370. ⟨10.1016/j.tet.2013.11.049⟩. ⟨hal-01498198⟩
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